Dyed cellulose esters or ethers and process of producing the dyeings



Patented Dec. 15, 1931 UNITED STATES PATENT OFFICE WILHELI ECKERT AND CARL ERICK Mfi'LLER, 0F FRANKFORT-ON-MAIN-HOCHST, GERMANY, ASSIGNORS TO GENERAL ANILINE WORKS, INC., 01 NEW YORK, N, Y., A

CORPORATION OF DELAWARE DYED C'ELLULOSE ESTERS OR ETHERS AND PROCESS OF PRODUCING THE DYEIN GS No Drawing. Application filed January 5, 1929, Serial- No. 330,613, and in Germany January 25, 1928.

The present invention relates to cellulose esters or others showing greenish-yellow tints and to a process of producing the dyeings.

We have found that derivatives, non-sulfonated in the nuclei, of 4-amino1.8-naphthalic acid of the following general formula:

I N 00 oo NH: wherein X stands for hydrogen, alkyl, aralkyl or an isocyclic hydrocarbon residue dye cellulose esters or ethers, especially acetate silk, valuable deep yellow tints having a greenish hue. The dyeings partly show a beautiful green fluorescence.

The cellulose esters or others can be dyed with the said naphthalic acid derivatives in the usual manner in a colloidal solution or an aqueous suspension, with or without the addition of a protective colloid, a salt, an acid or an alkali.

The 4-amino-L8-naphthalic acid derivatives of the above stated general formula are obtainable by causing t-amino-LS-naphthalic acid anhydride to react with ammonia or with an amine of the aliphatic or isocyclic series.

The following examples serve to illustrate our invention but are not intended to limit it thereto:

1) 1 kilo of acetate silk is dyed in a dyebath of 30-40 liters, containing 20 g. of the dyestufi' 4-amino-L8-naphthalic acid-ethyl imide of the formula:

| od bo Nil: in a finely subdivided form, for of an NH: there is likewise obtained a greenish-yellow dyeing of similar properties.

The compounds of the following constitutions yield similar dyeings on celluose esters and cellulose ethers, namely:

(1) the compound of the constitutional formula: on;

obtainable from 4-amino-L8-naphthalicacid-anyhydride and methylamine;

(2) the compound of the constitutional formula:

obtainable. from 4-an1ino-1.8-naphthalicobtainable from 4-2111)ino-1.8-naphthalicacid-anhydride and aniline; acid-anhydride and 4.6-dimcthyl-l-amino- (3) the compound of the constitutional benzene; formula: (7 the compound of the constitutional f formula on; Hz: /H: CH1 H1 |\Hl 10 N H N "l 1 Cl l0 us (I) O3 NH: obtainable from et-amino-1.8-naphthalicobtainable fr0m 441mm?L8-naphthalic' id h d id d l h l i ac1d-anhydr1de and 4.5-(11methyl-l-amino- :0 (4) the compound of the constitutional benzene; formula: CH3 (8) the compound of the constitutional formula: 25 Bic Q0111 N 00 bo f CO 30 w NHI:

obtainable from 4-amin0-1 8-n phtha1ic obtainable from 4-amino-1.8-naphthalic-acid- 35 acid-anhydride and 4-methyl-1-a1ninobenanhydride and 2.6-dimethyl-l-aminobenzene;

formula om zene; (9) the compound of the constitutional (5) the compound of the constitutional formula: on3

obtainable from Laminod smaphthah'o obtainable from et-amino-1.8-naphthalic-acidanh dride and 2.5-dimeth l-l-aminobenzene' 1 t y y I11(i;aI1hydIlCe and 5 methyl 1 aminoben the ompound of the cnnshitutlonai (6) the compound of the constitutional formula: formula: on, 4

w I a obtainable from 4-amino-L8-naphthalic acidanhydride and 2-chloro-l-aminobenzene; 1

(11) the compound of the constitutional formula obtainable from 4-amino-1.8-naphthalic-acidanhydride and o-chloro-l-aminobenzene;

(12) the compound of the constitutional formula:

Cl OH:

wherein X stands for hydrogen, alkyl, aralkyl or an isocyclic hydrocarbon residue.

2. The process which comprises dyeing an organic substitution product of cellulose with a compound, non-sulfonated in the nuclei, of the general formula:

wherein X stands for alkyl or aryl.

3. The process which comprises dyeing an organic substitution product of cellulose with a compound, non-sulfonated in the nuclei, of the general formula:

wherein X stands for alkyl or a phenyl residue.

4. The process which comprises dyeing an organic substitution product of cellulose with a compound of the general formula:

wherein Y stands for hydrogen or CH 5. The process which comprises dyeing an organic substitution product of cellulose with the 4-amino-1.8-naphthalic acid-4.6.-dimethyl-phenylimide of the formula:

' 6. Cellulose esters and ethers dyed with a 10. Cellulose esters and ethers dyed with a compound of the general formula: compound of the formula:

X OH:

I 6 N 70 06 E I OH:

N 7 1 00 Eo 7 wherein X stands for hydrogen, alkyl, arals so kyl or an isocyclic hydrocarbon residue.

7. Cellulose esters and ethers dyed with a po of the general formula: In test1mony whereof, we aflix our slgnatures. WILHELM ECKE RT. 1 CARL ERIOH'MULLER.

N 00 co wherein X stands for alkyl or aryl.

8. Cellulose esters and ethers dyed with a compound of the general formula:

l N 06 to l l whereln X stands for alkyl or phenyl.

9. Cellulose esters and ethers dyed with a compound of the general formula:

as N Y 65 wherein Y stands for hydrogen or CH 

